PD158780

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CAS:171179-06-9
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Products Intro: Product Name:N4-(3-Bromophenyl)-N6-methyl-pyrido[3,4-d]pyrimidine-4,6-diamine
CAS:171179-06-9
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  • 2020-02-01
  • CAS:171179-06-9
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PD158780 Basic information
Product Name:PD158780
Synonyms:N4-(3-Bromophenyl)-N6-methyl-pyrido[3,4-d]pyrimidine-4,6-diamine;Pyrido[3,4-d]pyriMidine-4,6-diaMine,N4-(3-broMophenyl)-N6-Methyl- (Related Reference);Pyrido[3,4-d]pyriMidine-4,6-diaMine,N4-(3-broMophenyl)-N6-Methyl-;PD 158780 solution;InSolution? PD 158780;PD 158780 - CAS 171179-06-9 - Calbiochem;InSolution PD 158780 - CAS 171179-06-9 - Calbiochem;PD 158780; PD-158780
CAS:171179-06-9
MF:C14H12BrN5
MW:330.18
EINECS:
Product Categories:
Mol File:171179-06-9.mol
PD158780 Structure
PD158780 Chemical Properties
Melting point 174.0 to 178.0 °C
Boiling point 499.6±45.0 °C(Predicted)
density 1.611±0.06 g/cm3 (20 ºC 760 Torr)
storage temp. Keep in dark place,Inert atmosphere,Store in freezer, under -20°C
solubility DMSO: ≥20mg/mL
form Yellow solid
pka5.80±0.30(Predicted)
color yellow
Safety Information
Hazard Codes Xn
Risk Statements 22
HS Code 2912.49.2600
MSDS Information
PD158780 Usage And Synthesis
UsesPD 158780 is a potent tyrosine kinase inhibitor of the epidermal growth factor receptor and has been shown to delay substantial growth of tumors in vivo tumor models.
DefinitionChEBI: PD158780 is a pyridopyrimidine that is pyrido[3,4-d]pyrimidine-4,6-diamine in which the amino groups at positions 4 and 6 are substituted by a m-bromophenyl group and a methyl group, respectively. It is a potent, cell-permeable, reversible ATP-competitive inhibitor of EGFR tyrosine kinase activity [IC50 values of 0.008, 49 and 52 nM for EGFR, ErbB2 (HER2) and Erb4 (HER4)]. It does not inhibit FGF or PDGF-mediated tyrosine phosphorylation. Induces G1 cell cycle arrest in MCF10A cells and is antiproliferative in A431 human epidermal carcinoma cells. It has a role as an antineoplastic agent and an EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor. It is a pyridopyrimidine, a secondary amino compound, a member of bromobenzenes, a diamine and an aromatic amine.
General DescriptionA potent inhibitor of the EGFR tyrosine kinase activity (8 pM). Also inhibits heregulin-stimulated autophosphorylation in SK-BR-3 (IC50 =49 nM) and MDA-MB-453 (IC50 = 52 nM) breast carcinomas. The inhibition is competitive and results from binding of the inhibitor at the ATP site of the enzymes. Inhibits the LPA-stimulated MAP kinase kinase 1/2 (MKK1/2) activation and EGFR tyrosine phosphorylation in HeLa and NIH3T3 cells.
Biological ActivityPotent inhibitor of ErbB receptor family tyrosine kinases (IC 50 values are 0.008, 49 and 52 nM for EGFR, ErbB2 and ErbB2/ErbB4 respectively) that does not inhibit FGF or PDGF-mediated tyrosine phosphorylation. Induces G 1 cell cycle arrest in MCF10A cells and is antiproliferative in A431 human epidermal carcinoma cells.
Biochem/physiol ActionsCell permeable: yes
Synthesis
N-(3-broMophenyl)-6-fluoropyrido[3,4-d]pyriMidin-4-aMine

171179-03-6

PD158780

171179-06-9

Example 60: Synthesis of N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine N-(3-Bromophenyl)-6-fluoro-pyrido[3,4-D]pyrimidin-4-amine (0.20 g, 0.63 mmol) was placed in a pressure vessel and an ethanol solution of methylamine was added and reacted at 100 °C. After completion of the reaction, purification was carried out by alumina column chromatography with the eluent dichloromethane/methanol (99:1, v/v) to afford the target product N4-(3-bromophenyl)-N6-methylpyrido[3,4-d]pyrimidine-4,6-diamine (0.07 g, 34% yield). 1H NMR (DMSO) δ 9.69 (1H, s), 8.75 (1H, s), 8.41 (1H, s), 8.21 (1H, brs), 7.93 (1H, brd, J = 7.6 Hz), 7.41-7.28 (2H, m), 7.06 (1H, s), 6.82 (1H, q, J = 5.0 Hz), 4.95 ( 3H, d, J = 5.0 Hz).

storageStore at -20°C
References[1] Patent: US5654307, 1997, A
PD158780 Preparation Products And Raw materials
Raw materialsN-(3-broMophenyl)-6-fluoropyrido[3,4-d]pyriMidin-4-aMine-->Ethanol-->Methylamine
Tag:PD158780(171179-06-9) Related Product Information
PD153035 HCl PD 98059 2-Bromopyridine Phenylimidazole 2-Phenylpyridine Pyridine PD158780

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